House Sitting for Robin Ch. 01

Story Info
He finds his hot friend's secrets & toys while spying.
4.2k words
4.08
39.5k
8

Part 1 of the 2 part series

Updated 09/22/2022
Created 07/28/2008
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Please feel free to send me an email at the address in my profile! Also don't copy and post on other web sites.

This is a multi part story and I'm posting part 1 and 2 on the same day. Part 3 should follow in three days.

I would like to thank Bengal52 for his many hours editing the story, and to Peter and Theresa for your help in pointing things out.

*

The following story might disturb you, but I found it my most erotic day of solitude.

I have to say that it's hard having a crush on a friend and even harder when she has a boyfriend. You see, I met this girl at work and we really hit it off. I'm not sure that she knows just how much I'm attracted to her. My attraction to her is way more then just physical and I have grown quite attached to her over the past two years. Yeah I want to bed her but I want her in my bed for the rest of our lives. Sorry the object of my affection, well her name is Robin.

A little over a year ago the company that I work for moved to Atlanta. Robin worked out of our Atlanta location and that is how we met. We hit it off and became part of her circle. I knew that she was with a guy, but didn't think much about him. Outside of work Robin was also friends with Elizabeth, Diane, and Pam.

We started to hang out and do things together. I knew that her boyfriend worked out of town and was only home for the weekends. Robin's boyfriends name is Taylor and for the most part he's a nice guy, just not the marrying type well everyone except Robin. A couple of times Robin has confessed that she wants to get married. In some ways I'm her work week boyfriend (except that we don't have sex) and on weekends Taylor is her real boyfriend. Robin loves to cook, drink wine, and even work out. During the week we would do just that, but on the weekends she would be with him.

Robin tells me everything, which is hard. She tells me how Taylor wants to do a threesome with another girl. The hard part is that Robin feels so inadequate when Taylor tells her these things. What does Robin do? She tries harder to please him. She tries to host the perfect dinner party, or make plans for the perfect weekend when all he's interested in is some hot sex.

Some days I just want to yell at her telling her to dump him! How can I do that? How can I tell her to dump him so that we can be together? Anything negative that I say will only make me look like a jealous ass. There were no options and I just had to face being in a crappy position. She would tell me the things he would say, all those little put downs that a lot of guys use.

Robin is about 5'10" and a size ten. We've gone shopping together. Personally I think that she loved to visit the higher-end clothing stores just to try on some expensive clothes. Every now and then she would purchase something. Our last trip was to Sak's Fifth Avenue, Robin made a comment about losing some weight and we made a pack on getting into shape together.

I'm 6'3" and in okay shape and do pretty well with the ladies. I'm not afraid to approach any woman and start a conversation. I don't expect anything when I meet someone new and hopefully will find a new friend and if things go well maybe a lover. Not all women like a guy like me; I'm two hundred fifty pounds with twenty inch arms and far from metro sexual. I like to look nice and dress in nice clothes.

What I enjoyed about our shopping trips was the time we spent together and when Robin was feeling good about herself she had a tendency to tease me. I think she enjoyed allowing her short skirt to rise up her thing while I drove back to her house after shopping.

Now some of your guys might think that Robin is a big girl but in no way is she fat. Trust me you only wished that you were lucky enough to see her in short skirts. Her legs are tone and Robin was blessed with an amazing rack.

Robin is a flirt and teases me relentlessly. What drives me nuts at work is when her nipples are hard. It's so hard to look at her eyes when we work together knowing that her nipples are rock hard which her nipples are almost always hard at work and I catch a lot of guys looking at them. I'm pretty sure that she knows others are looking. In my mind, I think she teases her nipples some times before we meet for drinks. I'm sure, like most women, she enjoys having the good looking men look at her.

I've seen quite a bit of her since Robin loves to flash. Can't tell you how many times when we would be at a bar and she would lift up her blouse and bra showing me her breasts. Then those summer nights when we were talking down by the lake, she just loved to lift up her shirt like it was normal for a girl's breasts to be exposed. There have been a few occasions where she's flashed her pussy. Last Tuesday we went to hooters and she enjoyed a few too many beers. Robin was wearing a jean mini skirt. She wanted to know if I found the Hooter's girls hot and right at our booth she pulled her thong off and handed it to me. On the way home Robin pulled up her skirt and asked me if I liked how she shaved her pussy.

My kind of girl! It's so hard to be that close and not suck on her tits when she's showing off the girls. One of these days, I'm going to be a little drunk and when she shows me her breasts I'm just going to drive right in.

One of the sexiest things any woman has ever done is this; Robin loves to give shots mouth to mouth. That is hard as a few times the shot has lead to a hot tongue kiss. Yeah, I wanted more. However, she was torn with her feelings for Taylor. I thinks Robin wanted to explore, but didn't want to harm her relationship.

About a year ago we both wanted to get in better shape and became work out buddies. Little did I know working out with her would become pure hell! Robin would dress pretty modestly when we worked out at the gym. However, we did get pretty close to each other when we spotted for one another. Just imagine how hard it was for me trying to bench press with her sanding over wearing tight shorts. I had to look close but swear to you that I could see her camel toe. More or less every workout became a sexy work out.

Once we left the gym things would be different. When we played tennis or run at night, she would dress a little sluttish. At night it's still humid and warm, we would run and start to sweat. Well, she almost always only wore a sports bra so I got to see a lot of her 36D tits since her nipples were hard all the time, some of her tops became nearly sheer when she sweated. I have to say it's hard running with a hard on.

Once Robin started to lose some weight she started to dress even sexier. When we first started to work together Robin never wore a dress. Now she only wore skirts to work. After work she loved to wear a semi sheer blouse with a lacy bra. My favorite were the wrap around skirts and imagine how it would be if she walked into my office and untied her dress asking me to take care of her.

With each milestone Robin met her skirts became shorter and shorter. Now she preferred to wear skirts that were five to six inches above her knee. In addition to that her jeans became a little lower on her hips. Now someone has to thank the person who invented low rider jeans. Every time she bends over to pick something up I would catch what color thong she was wearing.

I would go over to Robin's home everyday after work. Robin would make a comment about wanting to get into something more comfortable and run off to her bedroom to change. Only she would leave her bedroom door open and change. If we weren't working out she would come out wearing only a tee shirt without a bra. There were several times when I could see her walking around in her bedroom in her thong.

Some nights Robin's friend Elizabeth would join us. Elizabeth is married to Bob and Bob and Robin use to work together so that is how they know each other. Elizabeth is a free spirit and would show her breasts at the gym, while were playing tennis, and almost every dinner. Elizabeth was always trying to get everyone into the hot tub after working out and the idea sounded great. What Robin didn't like was that Elizabeth wanted everyone nude.

Anyway, here is where the story gets interesting. You see about a month ago Robin and Taylor won a three day cruise and she asked me to watch their house. They have three cats and the oldest needs to take medication at night. Being a friend I told her sure no problem.

Friday came and I went over to their house to take care of the cats. I fed the cats, gave out medication, and cleaned the litter box. I grabbed a beer and started to watch some TV. I don't know why but I checked out their DVD collection. I could only imagine Taylor watching porn on a Saturday night when Robin was sleeping. Then it hit me what if Robin liked porn? This is when things really started to go wrong, but I couldn't help myself. For some strange reason I felt a need to explore her home.

Then it hit me, I was alone and would be for three days. I had to learn more about her. We never talked about toys before but I bet that she had at least one vibrator. First was her dresser. Oh my god, she had lots of lingerie. Wonder if she wore it for Taylor? She had black, red, and white stockings. She had various teddies and some outfits. This girl knew how to dress for a man in bed! Funny thing is that I've never seen her wearing any hosiery even at work. I've seen her in some pretty short shorts when we worked out, but I could only imagine how her tone legs would look in stockings. At the bottom of the drawer she had some handcuffs, nipple clamps, nipple rings, a whip, and what looks like a clit clip. Wow, I had to watch her enjoy more of these toys.

I looked around her bedroom, her house was an older home, and I could easily wire up some surveillance equipment. My own private show! Before I started this job, I was a project manager for a security company. There I leaned everything about video equipment and how to hide things. I was hired for my programming skills and wrote several computer utilities to hack into spouses computers and monitor what he or she was doing online. At home I had all the equipment and everything was encrypted so that no one else could watch. In addition, the cameras had night vision, motion sensors, microphones, and I modified them so that the annoying red light was off. Not only could I watch Robin but I could also hear what she was saying.

Now, rule number one for spying is to make things invisible! Since today was only Friday I had two days to set things up.

I know what you're thinking. The first thing is what a perv going through her things and the other is that she would notice me snooping. However, I grew up in a house full of women and they taught me to fold and how to take care of intimates and secondly, could you blame me for peeking into her personal things?

Next I found the toy drawer. Oh my god, look at these toys! The first toy that I pulled out was a black life-like cock that was around nine inches long and two inches wide. Wow, I would love to have watched her take that thing. Next was a silver bullet. Oh, she had a rabbit. Wow, this had to be an anal plug due to it only being four inches long. Wow, even came with a remote! She had another bullet, a pocket vibrator, and a glass dildo. I never would have suspected Robin being so naughty!

She is my dream woman, I enjoy spending time with her, eating her food, and working out together. We get along very well and have become best friends. After looking through her bedroom confirmed that she was adventurous in bed. Why can't I find a woman that loves to dress up and enjoy toys? For the rest of the night all I could think about was watching her taking that nine inch black cock! Wonder if Taylor was that big or if she had a hung ex?

After finding her toys, I wondered if she had any naughty picture or some home movies!

Off to her computer!

I walked over to her home office and fired up her computer. Her computer came up to the normal windows XP screen without a password. Thank god that most people do not use a password for their home computer. In a way I kind of felt like one of those guys on CSI looking for clues. Needless to say that it didn't take long to find pictures and some home movies. Looks like Robin was a bad girl after all!

First thing that jumped out was all her pictures. She had two areas. It looks like the first one was for family and the other was of her and Taylor, or should I say her and then some pictures of her and Taylor together. Oh, she had a few folders with pictures of her and toys. I have to say that it was nice that they had organized the pictures into various folders. Oh, wait she was a picture of Robin kissing Elizabeth's nipple. Oh my, what naughty girl. The girls were in the hot tub and looks like Taylor was taking pictures.

The first movie was of her sucking Taylor while he held the camera. She looked so sexy taking his cock in her mouth. Right when he announced he was cumming, he pulled out and shot his load all over her face! Robin was nude, and after he finished Taylor walked around her making sure to capture everything. She looked so hot with his cum on her face. She grabbed a Kleenex and wiped her face dry. I looked down at her crotch to see Robin had a landing strip. How erotic, I always wondered if she shaved or had a landing strip. When you work out with someone and they wear sexy shorts every now and then I get a quick flash.

Second movie was of Taylor fucking Robin. Robin was on her back and holding the camera. Taylor would move so that she could capture his cock when he pulled out. Guess she had a little kink in her!

The next video was of Robin using her rabbit. Robin was nude and didn't try to hide a thing. Wow, that was hot! At first she was on her back, but then started to roll around on her bed. She looked directly into the camera while moving the rabbit down her body. Slowly she started to grind her pussy against the toy. With her other hand she reached down and turned the toy. She looked so sexy. Taylor moved the camera to get a close up on the rabbit entering Robin.

Needless to say that I was rock hard! I went back into her bedroom and grabbed a few things mainly a towel and some oil I had found with her toys. Then back to her office to watch Robin get laid by that big dildo. My cock was aching. I unzipped my shorts and stripped, sat back down in her chair and started to enjoy her personal movie. I worked my hand up and down my cock trying to mimic the way she was fucking herself with the dildo. She had the thing deep in her wet pussy and the nub was pressed against her clit. Looked to me that the nub vibrates and that's what gets a woman off. Robin looked so hot cumming but part of me felt empty due to the experience not being real.

The next movie was Robin in her bedroom and nude. She had the life like dildo and her silver bullet next to her. Taylor was moving around the room and they two of them were enjoying some dirty talk. Robin was talking about being at a club and two men hitting on her. She talked about how sexy she felt having the attention of two men.

Hearing her, watching her was too much. My hand worked up and down my cock. I loved how my cock felt, all firm and thick. The skin tight, the tip of my cock was very sensitive as I came closer and closer to reaching my orgasm.

Robin talked about taking the guys into the alley, being bent over the hood of a car, and how each man took their turn fucking her. The way she said it, oh I could only imagine how erotic it would be watching her getting fucked by two strangers and just that thought, rippled though my body. I looked down to see a large white stream of cum shoot out of my cock, landing on the floor below me.

Wow that didn't take me long. I felt so kinky after cumming in her home. I grabbed the towel and cleaned myself up, then made sure that I didn't leave anything behind. Was it really wrong masturbating while watching her ride that life like dildo?

I imagined it was my cock that she was riding, and for a second time my cock hard and I swear it could bend steel. The skin so tight and I felt like I was going to explode. Back to her computer to find a new movie and hit pay dirt. Robin was walking around her house, wearing her black pumps. She had the life like dildo in hand as she looked for the perfect place to get off at.

At the base of the toy was a suction cup that she placed the toy on the corner on the coffee table and then she rode it like she was doing a guy. It was so erotic seeing that toy on her table, Robin walking around the room nude, and then to watch her mount it. Slowly she lowered herself onto the dildo. Inch by inch she took that cock into her wet pussy. Talk about mix emotion watching her. Sure part of me knew that this was wrong but how could I stop watching now? Taylor got some pretty hot close ups of her clit and then moved behind her and took some more close ups. Some women use toys just to please the man in her life, but Robin looked like she was really enjoying herself. Needless to say Robin looked hot! My hot friend was nude and riding a toy like it was her lover. I've never watched a friend having sex before and I have to say that this was totally hot! She rode that thing to a very powerful orgasm.

When Robin leaned back and started slowed down, Taylor had turned the vibrator part up while she slowly moved up and down all nine inches. Robin started to become very vocal and quickly came. While I watched her cum, I shot a large stream of cum! I knew that I was close, but hearing her cum just pushed me over the edge. Watching her cum sent me over the edge and I shot a large stream of cum that landed on her desk. Thank god it missed her keyboard!

For a second time today, I had taken care of my needs, so I cleaned myself up and made sure that everything was back in its proper place. Then I went back to her office and sat at her desk.

I grabbed my thump drive and installed a little utility on her desktop and laptop. The utility allowed me to access her computer any time her computer was on and connected to the internet. Robin's desktop had a nice webcam and her laptop had one built in. So with a little tweaking of my utility I could watch her without her knowing. After installing the utility, I copied her movies and pictures to my thumb drive.

To me I find it very erotic to know that I can watch her at any time without her knowing. My dream would be to watch her masturbating while she talked to him. Since Taylor spends the week out of town, maybe they use the webcam to take care of personal needs. Well I can only hope!

I almost left without giving her old cat her medication. That shows how much my mind was racing. Would I see her having sex? Does Robin webcam with Taylor or other men? Oh what if she did webcam with other men?

Saturday started out like every other day but by me being a little naughty my life became a little more interesting! Now I had something to look forwarded to! I had to see more, see what all went on in her house.

After breakfasts I planned Operation Robin.

My plan was to install several cameras at key locations and in such a way that she would have no clue. I didn't want to plug the cameras into her router as that would be obvious. I placed a router in her attic out of visual sight then plugged the cameras into the router, and finally the router directly into her cable line. The images would be encrypted so that no one else could view them. Once everything was packed I was ready to install all the equipment. When a camera detected motion my computer would send a text to my cell. This way I didn't have to sit at my computer and wait for action. I had enough storage space at my home for a weeks worth of video. I could capture any hot action and delete all the non action feeds.

12